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 Summary 

 Beraisa: One who builds a sukkah for his use recites a shehechyanu [this bracha is actually for the whole Yom Tov. It may be made already at the time of building the sukkah]. When he enters it on Yom Tov, he recites leisheiv basukkah. 

If the sukkah is already built, he may recite the bracha if he renews something in its construction, otherwise he can recite it when he enters it on Yom Tov.

 Rav Ashi: I saw Rav Kahana make all the blessings on the kos of kiddush [this is our minhag as well, so as not to confuse some people who have a built sukkah all year round].

 Beraisa: If one has several mitzvos before him, he can lump them together in one bracha “Asher kidshanu b’mitzvosav v’tzivanu al hamitzvos”. 

 Rabbi Yehuda: Each mitzvah should get its own bracha [for more on this, see the lashon kodesh maamar here]. https://groups.google.com/a/torasavigdor.org/g/toras-avigdor-ey/c/GSRU628fWrQ/m/oFPXQB4UAQAJ 

 Rabbi Zeira and some say Rabbi Chanina bar Papa: We follow Rabbi Yehuda. 

 Rabbi Zeira and some say Rabbi Chanina bar Papa: The reason for this is because the possuk says “Blessed is Hashem every day”. Is Hashem not blessed at night? It means every day should get the blessing appropriate for that day (every season deserves its own thanks. In the summer we’re grateful that we save on heating costs). Similarly, each mitzvah should get its own blessing.

 Rabbi Zeira and some say Rabbi Chanina bar Papa: The way of Hakodosh Boruch Hu is not the way of human beings. The way of human beings is that if something is empty it can be filled but if it’s full it can no longer be filled. But the way of Hakodosh Boruch Hu is that someone full can be filled with even more (if his mind is filled with Hashem, then there’s room for more), but if he’s an empty man he cannot accept anything.

This is based on the possuk “If you listened, you will listen”.

 Another pshat: “If you listen to the old, you’ll hear new” (one explanation is that if you’ll review the old things, you’ll gain new understanding of the old things. Another explanation is that if you listen to old things, Hashem will give you more opportunity to hear new things). But if you don’t listen to the old, you won’t hear.